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Illustrative Central Florida lakeside estate with mature oaks, palms and landscaped grounds beside calm water in warm evening light.

Your primary or second home

Windermere homes for sale: luxury homes

Compare Windermere luxury homes for sale with our team. Review the actual property, setting and ownership costs.

Explore Windermere’s Luxury Communities

  • Isleworth

    Estate homes among the Butler Chain of Lakes, with an extensive private golf, sporting and social club environment.

  • Keene’s Pointe

    A gated community of villages around lakes and golf, with distinct golf and social membership options at the Golden Bear Club.

  • Lake Butler Sound

    A gated estate-home community beside Lake Butler, with waterfront properties among the choices.

  • Waterstone

    A gated setting on Lake Butler’s shores for buyers prioritizing a lake-oriented residential location.

  • Casabella at Windermere

    Gated single-family estate homes in West Orange County, originally planned with approximately half-acre homesites.

  • Reserve at Belmere

    Guard-gated living with shared fitness, court sports, a playground and a lakefront gazebo and boardwalk.

Featured Windermere Communities

Explore Isleworth, Keene’s Pointe, Lake Butler Sound and Chaine du Lac, with links to each community’s homes and buyer guide.

Browse Windermere Luxury Homes by Price

Explore homes by asking price, starting at $1 million.

Luxury Homes for Sale in Windermere

67 listings

Market snapshot of the searched areas

Area-wide public inventory checked 31 October 2026. Compare each area separately; their boundaries can overlap.

  • Isleworth: null properties for sale; median asking price not available.
  • Keene's Pointe: null properties for sale; median asking price not available.
  • Lake Butler Sound: null properties for sale; median asking price not available.
  • Lake Butler Boulevard: null properties for sale; median asking price not available.
  • Downtown Windermere: null properties for sale; median asking price not available.

Nearby sold homes for comparison

11 properties sold within half a mile in the last 12 months · median $556,000

Isleworth: Estate Homes and Private Club Living

Windermere homes for sale include different price points and settings; this page focuses on Windermere luxury homes for sale. We help you compare architecture, usable space, condition and ownership costs. This selection combines five saved areas: Isleworth, Keene’s Pointe, Lake Butler Sound, Lake Butler Boulevard and Downtown Windermere. Keep each community's club arrangements and documented waterfront rights separate.

If you are comparing Windermere luxury homes with a substantial private-club offering, Isleworth brings estate homes together with a 600-acre golf-community setting among the Butler Chain of Lakes. Its 18-hole championship course was originally designed by Arnold Palmer and later enhanced by Steve Smyers. Beyond golf, club facilities include dining, fitness and spa facilities, tennis, padel and a pool overlooking Lake Louise. That range gives you more to consider than the course alone, particularly if different members of your household enjoy different activities. Confirm membership arrangements separately: these club facilities and members-only docks are not benefits to assume automatically accompany a home purchase.

Explore Isleworth homes for sale.

Explore Isleworth homes for sale

Keene’s Pointe: Village Settings and Golf

Keene’s Pointe is a gated residential community arranged across 18 villages among the Butler Chain of Lakes and its golf course. The Golden Bear Club centers on an 18-hole Jack Nicklaus Signature course, while clubhouse dining provides another reason to participate beyond a round of golf. Golf and social memberships are distinct, with social amenities encompassing dining, tennis, swimming and fitness. Consider which activities you would use throughout the week, or during time at a second home, before weighing the club offering. Review membership separately from association obligations, and compare each property’s position carefully: a home in this lake-oriented community does not necessarily have lake frontage.

Explore Keene’s Pointe homes for sale.

Explore Keene’s Pointe homes for sale

Lake Butler Sound: A Lake-Oriented Estate Setting

Lake Butler Sound offers a gated estate-home setting beside Lake Butler, with waterfront properties among its residential choices. Here, start your comparison with the home and its grounds: the layout, outdoor space and relationship to the water matter more than assuming a country-club package. Cartmel Gardens adds an English-garden element to the community’s character. If lakefront living is your priority, distinguish direct frontage from a water view and establish what access belongs to the individual property. For a primary or second home, that approach helps you judge how the setting would support time outdoors and everyday use.

Explore Lake Butler Sound homes for sale.

Illustrative Florida estate garden with clipped hedges, a curving stone path and mature trees overlooking a tranquil lake.
Explore Lake Butler Sound homes for sale

Chaine du Lac: Another Community to Explore

Include Chaine du Lac in your Windermere shortlist and compare individual homes against your priorities for layout, outdoor space and everyday living. We can help you review available properties and identify the questions to ask about each home’s setting, association obligations and ownership arrangements.

Explore Chaine du Lac homes for sale

More Communities to Add to Your Shortlist

As you compare luxury homes in Windermere, Florida, these communities add lake-oriented settings, larger homesites and shared recreation to the mix.

AspectCommunityResidential settingDistinguishing featureWhat to compare
WaterstoneWaterstoneA gated residential community on the shores of Lake Butler in the Windermere area.A lake-oriented setting to consider if proximity to the water is central to your search.Compare each home’s waterfront position, water views and documented dock access separately.
CasabellaCasabella at WindermereA gated single-family estate-home community in West Orange County, with an emphasis on residential space.Originally planned with approximately half-acre homesites, offering a lot-size comparison beyond golf or waterfront.Check actual parcel size, usable outdoor space and how the home sits on its grounds.
Reserve at BelmereReserve at BelmereA guard-gated residential community with a lakefront gazebo and boardwalk for relaxation and fishing.Shared fitness, tennis, pickleball, basketball, beach volleyball and a playground.Consider which shared recreation facilities you would use regularly, rather than prioritizing on-site golf.

Everyday Living in the Windermere Area

Choosing a luxury home in Windermere, Florida, also means considering the routines beyond your front door. For a broader look at the area and its property choices, explore our guide to Windermere real estate and homes for sale. The Friday farmers market at Town Square Park offers a local outing to build into your week. The wider Windermere-address area extends beyond the incorporated town, so check each property’s jurisdiction when comparing services and town-resident amenities. For a primary home, consider the journeys and activities that shape an ordinary week. For a second home, think about how you want to spend your time there and which community facilities you would genuinely use.

Explore Windermere on the Map

Use the map to orient your search. Check each home’s location and jurisdiction, as a Windermere address can extend beyond the town boundary.

FAQs About Buying Luxury Homes in Windermere

Gaby Sadler, Property Specialist

Gaby Sadler

Property Specialist, Serhant

Find Windermere luxury homes for sale with Gaby

Tell me your budget and plans. I'll help compare Windermere homes for sale in this luxury search, including the actual layout, condition and ownership obligations.

Find the Right Windermere Community for You

Your shortlist should reflect how you want to live, whether that means regular club participation, a lakefront setting, larger grounds or shared recreation close to home. We can help you compare those priorities across Windermere’s communities and narrow your property search. Explore homes for sale, then look closely at the setting and ownership arrangements behind each choice.

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